Fevipiprant

• CAT Number: I005253
• CAS Number: 872365-14-5
• Molecular Formula: C₁₉H₁₇F₃N₂O₄S
• Molecular Weight: 426.41
• Purity: ≥95%
• Target: CRTh2 receptor antagonist
• Solubility: DMSO ≥ 32 mg/mL
• Storage: Store at -20°C
• IUPAC Name: 2-[2-methyl-1-[[4-methylsulfonyl-2-(trifluoromethyl)phenyl]methyl]pyrrolo[2,3-b]pyridin-3-yl]acetic acid
• InChI: InChI=1S/C19H17F3N2O4S/c1-11-15(9-17(25)26)14-4-3-7-23-18(14)24(11)10-12-5-6-13(29(2,27)28)8-16(12)19(20,21)22/h3-8H,9-10H2,1-2H3,(H,25,26)
• InChIKey: GFPPXZDRVCSVNR-UHFFFAOYSA-N
• SMILES: CC1=C(C2=C(N1CC3=C(C=C(C=C3)S(=O)(=O)C)C(F)(F)F)N=CC=C2)CC(=O)O

Fevipiprant (Cat.No:I005253) is a selective antagonist of the prostaglandin D2 receptor subtype 2 (DP2 or CRTh2). It is used in the treatment of asthma, particularly in patients with severe eosinophilic asthma. Fevipiprant helps reduce airway inflammation and improve lung function by blocking the DP2 receptor, which is involved in allergic and inflammatory responses.

Reference

1:Discovery of Fevipiprant (NVP-QAW039), a Potent and Selective DP2 Receptor Antagonist for Treatment of Asthma. Sandham DA, Barker L, Brown L, Brown Z, Budd D, Charlton SJ, Chatterjee D, Cox B, Dubois G, Duggan N, Hall E, Hatto J, Maas J, Manini J, Profit R, Riddy D, Ritchie C, Sohal B, Shaw D, Stringer R, Sykes DA, Thomas M, Turner KL, Watson SJ, West R, Willard E, Williams G, Willis J.ACS Med Chem Lett. 2017 Apr 25;8(5):582-586. doi: 10.1021/acsmedchemlett.7b00157. eCollection 2017 May 11. PMID: 28523115
2:Absorption, distribution, metabolism and excretion of the oral prostaglandin D2 receptor 2 (DP2) antagonist fevipiprant (QAW039) in healthy volunteers and in vitro. Pearson D, Weiss HM, Jin Y, van Lier JJ, Erpenbeck VJ, Glaenzel U, End P, Woessner R, Eggimann F, Camenisch G.Drug Metab Dispos. 2017 Apr 25. pii: dmd.117.075358. doi: 10.1124/dmd.117.075358. [Epub ahead of print] PMID: 28442499
3:Data on the oral CRTh2 antagonist QAW039 (fevipiprant) in patients with uncontrolled allergic asthma. Erpenbeck VJ, Popov TA, Miller D, Weinstein SF, Spector S, Magnusson B, Osuntokun W, Goldsmith P, Weiss M, Beier J.Data Brief. 2016 Aug 29;9:199-205. doi: 10.1016/j.dib.2016.08.039. eCollection 2016 Dec. PMID: 27656673 Free PMC Article
4:Fevipiprant, a prostaglandin D2 receptor 2 antagonist, in patients with persistent eosinophilic asthma: a single-centre, randomised, double-blind, parallel-group, placebo-controlled trial. Gonem S, Berair R, Singapuri A, Hartley R, Laurencin MF, Bacher G, Holzhauer B, Bourne M, Mistry V, Pavord ID, Mansur AH, Wardlaw AJ, Siddiqui SH, Kay RA, Brightling CE.Lancet Respir Med. 2016 Sep;4(9):699-707. doi: 10.1016/S2213-2600(16)30179-5. Epub 2016 Aug 5. PMID: 27503237
5:The oral CRTh2 antagonist QAW039 (fevipiprant): A phase II study in uncontrolled allergic asthma. Erpenbeck VJ, Popov TA, Miller D, Weinstein SF, Spector S, Magnusson B, Osuntokun W, Goldsmith P, Weiss M, Beier J.Pulm Pharmacol Ther. 2016 Aug;39:54-63. doi: 10.1016/j.pupt.2016.06.005. Epub 2016 Jun 21. PMID: 27354118
6:Pharmacokinetics, Safety, and Tolerability of Fevipiprant (QAW039), a Novel CRTh2 Receptor Antagonist: Results From 2 Randomized, Phase 1, Placebo-Controlled Studies in Healthy Volunteers. Erpenbeck VJ, Vets E, Gheyle L, Osuntokun W, Larbig M, Neelakantham S, Sandham D, Dubois G, Elbast W, Goldsmith P, Weiss M.Clin Pharmacol Drug Dev. 2016 Jul;5(4):306-13. doi: 10.1002/cpdd.244. Epub 2016 Mar 28. PMID: 27310331 Free PMC Article
7:Fevipiprant (QAW039), a Slowly Dissociating CRTh2 Antagonist with the Potential for Improved Clinical Efficacy. Sykes DA, Bradley ME, Riddy DM, Willard E, Reilly J, Miah A, Bauer C, Watson SJ, Sandham DA, Dubois G, Charlton SJ.Mol Pharmacol. 2016 May;89(5):593-605. doi: 10.1124/mol.115.101832. Epub 2016 Feb 25. PMID: 26916831 Free Article
8:Synthesis of a high specific activity methyl sulfone tritium isotopologue of fevipiprant (NVP-QAW039). Luu VT, Goujon JY, Meisterhans C, Frommherz M, Bauer C.J Labelled Comp Radiopharm. 2015 May 15;58(5):188-95. doi: 10.1002/jlcr.3281. Epub 2015 Apr 16. PMID: 25881897